AVORELIN ACETATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C65H85N17O12.C2H4O2
Molecular Weight	1356.5291
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(O)=O.CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC2=C(C)NC3=C2C=CC=C3)NC(=O)[C@H](CC4=CC=C(O)C=C4)NC(=O)[C@H](CO)NC(=O)[C@H](CC5=CNC6=C5C=CC=C6)NC(=O)[C@H](CC7=CN=CN7)NC(=O)[C@@H]8CCC(=O)N8

InChI

InChIKey=MQOAHMYIJGUWMT-JESVGHGASA-N

InChI=1S/C65H85N17O12.C2H4O2/c1-5-69-63(93)54-17-11-25-82(54)64(94)47(16-10-24-70-65(66)67)75-57(87)48(26-35(2)3)76-61(91)52(30-43-36(4)73-45-15-9-7-13-42(43)45)80-58(88)49(27-37-18-20-40(84)21-19-37)77-62(92)53(33-83)81-59(89)50(28-38-31-71-44-14-8-6-12-41(38)44)78-60(90)51(29-39-32-68-34-72-39)79-56(86)46-22-23-55(85)74-46;1-2(3)4/h6-9,12-15,18-21,31-32,34-35,46-54,71,73,83-84H,5,10-11,16-17,22-30,33H2,1-4H3,(H,68,72)(H,69,93)(H,74,85)(H,75,87)(H,76,91)(H,77,92)(H,78,90)(H,79,86)(H,80,88)(H,81,89)(H4,66,67,70);1H3,(H,3,4)/t46-,47-,48-,49-,50-,51-,52+,53-,54-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C2H4O2
Molecular Weight	60.052
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C65H85N17O12
Molecular Weight	1296.4771
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	3
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10569560
Curator's Comment: description was created based on several sources, including: DOI: 10.1023/A:1008898216113 | https://www.ncbi.nlm.nih.gov/pubmed/16939388

Avorelin is a superagonist of natural luteinizing-hormone-releasing-hormone. Avorelin has been formulated in high molecular weight polylactic glycolic acid to afford protracted and continuous release of the peptide from subcutaneous implants. Avorelin has been in phase II clinical trials by Mediolanum for the treatment of prostate cancer, breast cancer and endometriosis. However, this research has been discontinued. Adverse events mainly related to androgen suppression (hot flushes, decreased libido and impotence) or the nature of the disease (skeletal pain).

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Gonadotropin-releasing hormone receptor 41 Target ID: CHEMBL1855 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16939388 \| DOI: 10.1023/A:1008898216113	Agonist 2752

Conditions

Condition	Modality	Highest Phase	Product
Prostate cancer 186 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10569560 DOI: 10.1023/A:1008898216113	Primary	Phase II 1147	Unknown Approved Use Unknown
Breast cancer 432 Sources: https://www.pharmacodia.com/yaodu/html/v1/chemicals/b9978645dcddd6ff72f77cf90e6f4bd5.html	Primary	Phase II 1147	Unknown Approved Use Unknown
Endometriosis 32 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16939388 https://www.pharmacodia.com/yaodu/html/v1/chemicals/b9978645dcddd6ff72f77cf90e6f4bd5.html	Primary	Phase II 1147	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Pharmacodynamics of a long acting depot preparation of avorelin in patients with prostate cancer. Avorelin Study Group.	1999-12	10569560
Manipulation of postnatal testosterone levels affects phallic and clitoral development in infant rhesus monkeys.	1999-04	10194644
Investigation of the role of postnatal testosterone in the expression of sex differences in behavior in infant rhesus macaques (Macaca mulatta).	1999-04	10202126

Patents

Sample Use Guides

In Vivo Use Guide

10 or 15 mg implants

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:15:12 GMT 2025` Edited by `admin` on `Mon Mar 31 18:15:12 GMT 2025`
Record UNII	3575L4873R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AZD-5928

Preferred Name

English

AVORELIN ACETATE

Common Name

English

1-9-LUTEINIZING HORMONE-RELEASING FACTOR (SWINE), 6-(2-METHYL-D-TRYPTOPHAN)-9-(N-ETHYL-L-PROLINAMIDE)-, ACETATE (SALT)

Common Name

English

5-OXOPRO-HIS-TRP-SER-TYR-ME-TRP-LEU-ARG-PRO-N-ETHYLAMIDE ACETATE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1910